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Record Information
Version1.0
Creation Date2016-09-30 22:19:28 UTC
Update Date2020-06-04 20:35:57 UTC
MCDB ID BMDB0000086
Secondary Accession Numbers
  • BMDB00086
Metabolite Identification
Common NameGlycerophosphocholine
DescriptionGlycerophosphocholine, also known as GPC or choline alfoscerate, belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position. Glycerophosphocholine exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Glycerophosphocholine exists in all living species, ranging from bacteria to humans. Glycerophosphocholine participates in a number of enzymatic reactions, within cattle. In particular, Glycerophosphocholine can be biosynthesized from 11-cis-retinol and PC(24:1(15Z)/15:0); which is mediated by the enzyme lecithin retinol acyltransferase. In addition, Retinyl ester and glycerophosphocholine can be biosynthesized from vitamin a and PC(24:1(15Z)/15:0) through its interaction with the enzyme lecithin retinol acyltransferase. In cattle, glycerophosphocholine is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
Synonyms
ValueSource
2-[[(2,3-Dihydroxypropoxy)hydroxyphosphinyl]oxy]-N,N,N-trimethyl-ethanaminium inner saltHMDB
a-GlycerophosphorylcholineHMDB
a-GlycerylphosphorylcholineHMDB
alpha-GlycerophosphorylcholineHMDB
alpha-GlycerylphosphorylcholineHMDB
Choline alfoscerateHMDB, MeSH
Choline glycerophosphateHMDB
Glycerol 3-phosphocholineHMDB, MeSH
Glycerol phosphorylcholineHMDB
Glycerol-3-phosphatidylcholineHMDB
GlycerophosphatidylcholineHMDB
GlycerophosphorylcholineHMDB, MeSH
GPCHMDB
GPChoHMDB
Hydrogen glycerophosphate cholineHMDB
L-alpha-GlycerophosphocholineHMDB
L-alpha-GlycerophosphorylcholineHMDB
L-alpha-GlycerylphosphorylcholineHMDB, MeSH
L-Choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner saltHMDB
sn-glycero-3-PhosphocholineHMDB
Alfoscerate, cholineMeSH, HMDB
Choline alphoscerateMeSH, HMDB
Glycerophosphate, cholineMeSH, HMDB
Alphoscerate, cholineMeSH, HMDB
L alpha GlycerylphosphorylcholineMeSH, HMDB
3-Phosphocholine, glycerolMeSH, HMDB
Glycerol 3 phosphocholineMeSH, HMDB
GlycerylphosphorylcholineMeSH, HMDB
CeretonHMDB
CholicerinHMDB
CholitilineHMDB
DelecitHMDB
GliatilinHMDB
Glycerol 3-phosphorylcholineHMDB
GlycerophosphocholineHMDB
Glycerophosphoric acid choline esterHMDB
Glyceryl 3-phosphorylcholineHMDB
GlycerylphosphocholineHMDB
L-alpha-GPCHMDB
L-α-GPCHMDB
L-α-GlycerophosphocholineHMDB
L-α-GlycerophosphorylcholineHMDB
L-α-GlycerylphosphorylcholineHMDB
O-(sn-glycero-3-Phosphoryl)-cholineHMDB
sn-glycero-3-PhosphorylcholineHMDB
α-GlycerophosphorylcholineHMDB
α-GlycerylphosphorylcholineHMDB
Chemical FormulaC8H20NO6P
Average Molecular Weight257.2213
Monoisotopic Molecular Weight257.102823889
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number28319-77-9
SMILESNot Available
InChI Identifier
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1
InChI KeySUHOQUVVVLNYQR-QMMMGPOBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentGlycerophosphocholines
Alternative Parents
Substituents
  • Glycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • 1,2-diol
  • Secondary alcohol
  • Organic nitrogen compound
  • Organic salt
  • Hydrocarbon derivative
  • Primary alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified284 - 1460 uM details
Detected and Quantified395 - 1217 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified669 +/- 53 uM details
Detected and Quantified659 +/- 8 uM details
Detected and Quantified646 +/- 21 uM details
Detected and Quantified705 +/- 45 uM details
Detected and Quantified532 +/- 108 uM details
Detected and Quantified532 +/- 240 uM details
Detected and Quantified617 +/- 84 uM details
HMDB IDHMDB0000086
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-GPC
METLIN IDNot Available
PubChem Compound71920
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceEvans, Christopher Thomas; McCague, Raymond; Tyrrell, Nicholas David. Preparation of phospholipid-intermediate glycerophosphocholine by a crystallization process. PCT Int. Appl. (1993), 8 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  4. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  5. Maher AD, Hayes B, Cocks B, Marett L, Wales WJ, Rochfort SJ: Latent biochemical relationships in the blood-milk metabolic axis of dairy cows revealed by statistical integration of 1H NMR spectroscopic data. J Proteome Res. 2013 Mar 1;12(3):1428-35. doi: 10.1021/pr301056q. Epub 2013 Feb 21. [PubMed:23394630 ]
  6. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  7. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23. [PubMed:28342601 ]
  8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  9. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.